Ethanol → HCID 69214137, compound

HRID 2221562Notes

Reaction equation

HRID 2221562 reaction equation
[CH:1]([C:3]1[CH:26]=[CH:25][C:6]([O:7][CH2:8][C:9]2[N:10]=[C:11]([C:15]3[CH:24]=[CH:23][CH:22]=[CH:21][C:16]=3[C:17]([O:19][CH3:20])=[O:18])[O:12][C:13]=2[CH3:14])=[C:5]([O:27][CH3:28])[CH:4]=1)=[O:2].C(O)C.[BH4-].[Na+].O>O1CCCC1>[OH:2][CH2:1][C:3]1[CH:26]=[CH:25][C:6]([O:7][CH2:8][C:9]2[N:10]=[C:11]([C:15]3[CH:24]=[CH:23][CH:22]=[CH:21][C:16]=3[C:17]([O:19][CH3:20])=[O:18])[O:12][C:13]=2[CH3:14])=[C:5]([O:27][CH3:28])[CH:4]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 4311764Sodium borohydrideHCID 86605712HCID 86605712, compound

Product 1

HCID 69214137HCID 69214137, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-{4-[(4-formyl-2-methoxyphenoxy)methyl]-5-methyl-1,3-oxazol-2-yl}benzoate (1.30 g) in tetrahydrofuran (20 mL)-ethanol (10 mL) was gradually added sodium borohydride (0.13 g) at room temperature. After stirring for 2 hrs, water was added to the reaction mixture and the precipitated crystals were collected by filtration to give methyl 2-{4-[(4-hydroxymethyl-2-methoxyphenoxy)methyl]-5-methyl-1,3-oxazol-2-yl}benzoate as colorless crystals (1.20 g, yield 92%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 100-101° C.

Workup

  1. customat room temperature
  2. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-901bdd78f5fd4c9d960a9f7e8ce78837
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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